I think the worst I have done is drop $100 at a sushi bar... but it was worth it... unfortunately I have a taste for very expensive sake.
I also just spent $140 on two eighteen year old bottles of scotch, ouch!
FWIW Porsche-O-Phile seems like a nice guy and is probably off line. I wouldn't be surprised if he offers an apology as soon as he reads the rest of this thread.